Hi, , I’m Kathy. I’m a two-time CEO and COO who writes about leadership, career, and mindset with the vulnerability and practicality I craved when I was in the seat. I coach leaders who are ambitious, successful, and caring, and who know they need support and aren’t afraid to ask for it. So glad you’re here.
I walked through the grass, excited to get on with my day. I tripped and almost face-planted. I’m pretty uncoordinated, but I didn’t misstep this time. It wasn’t a rock or an incline. It was my shoe.
The front strap had broken. I was heartbroken. This was my favorite sandal. It had carried me through years of pounding the pavement in NYC through hard days and long trips. Multiple cobbler repairs had already exceeded the original cost, yet I refused to let go, even when the soles were cracked and the ankle strap had broken only the previous summer.
It reminded me of several clients who had worked hard a few years ago to find the right role through a careful, thoughtful search, but were now finding the job no longer fit. Industry dynamics shifted; fellow leaders revealed less-than-favorable leadership traits; a strategy that sounded good earlier proved much harder to execute.
And yet, like me, they continue to want to make the shoe fit.
It didn’t even occur to me that my shoe would actually break before I could get into my car and head home. Luckily, I wasn’t far. My hobbling didn’t feel too embarrassing since no one was there to watch me, and I didn’t sustain further injury, just grief from losing a favorite shoe.
But a senior-level role is not a shoe.
When it breaks, you aren’t hobbling alone to the car. Your team, your board, and your reputation are all watching. And it may break on someone else’s timeline, not yours.
The signs often start as noise.
Beth is a Chief Product Officer with deep experience across several tech industries. She joined a small startup three years ago with the promise of additional capital raises and ultimately an IPO or acquisition.
She knew it was risky, but she knew what mattered to her was worth the risk. She was excited about the target customer, the value proposition, and the leadership team. It was her first time in the C-Suite, and she had been hungering for a seat at the table for years.
Fast forward two years and the market had shifted. Customers who once had a clear need were now scrambling and adjusting budgets to cover other business risks. The company struggled to find a strong commercial leader. The sales pipeline was weak, and the internal operations were weaker.
To cap it off, the CEO, Mark, had started to micromanage everyone, including Beth. It was one of her most essential criteria: to avoid working with someone who couldn’t relinquish control. She had worked for those bosses before, and it was a non-starter. The interview process and the first year raised no flags.
But starting in the middle of year two, when the numbers were behind, Mark started to ask for more reports. Then he started asking to join some of her team meetings. Before long, Mark wasn’t just reviewing the product roadmap; he was sitting alongside some of Beth’s team to review research and test results.
Beth bristled. In her mind, the commercial team was the bigger problem, and the CEO seemed to be ignoring it. Instead of raising it with him, she gave Mark grace. He had a newborn at home, and clearly cared. She chalked it up to the moment and told herself it would pass.
It didn’t.
Making the call to start a job search is often harder than the search itself.
For Beth, the decision to start anew is fraught.
She has two young children, and she and her partner are contemplating a third. She’s afraid of tethering herself to the proverbial sinking ship. She knew the risk when she joined; she wasn’t naive. But now that she’s facing it, she doesn’t know if she has the energy and stamina to start a search while working long startup hours and parenting. Add the risk that the new role isn’t all roses and sunshine, and it comes down to whether you stay with the devil you know or roll the dice on one you don’t.
It’s similar to my attachment to my shoe. It fit my needs for so long. I wasn’t ready to recognize it could no longer serve my purpose because I had decided it wasn’t worth searching for another that probably didn’t exist or would never be as good.
It’s a very pessimistic outlook.
But it’s all too common because it’s filled with truths mixed with fears.
While situations differ, this is the most common challenge I hear from senior leaders who aren’t happy in their current role. They are starting to see the signals, but they don’t know if it’s worth the switching costs.
And for some leaders, there are bigger questions about what to even search for.
While many are clear on their industry focus or functional specialty, others are either generalists or dabbling with the idea of switching. Perhaps they want to try a high-growth sector. Or they are bored with their current function.
Coupled with the richness and responsibilities of midlife, these questions trap us. We lose all sense of possibility and replace it with dread.
You don’t have to hold yourself hostage.
The only thing worse than making the wrong decision is delaying it while letting it drain you.
Indecision is simply a passive decision not to move forward. It’s the same as saying I’ll stay for now. That’s a fine choice; it might even be the best choice. But it won’t feel that way if you don’t actively choose it. Choosing to stay, on purpose and with a date to look again, is a real decision.
I’m not a fan of forcing actions when you aren’t ready. Instead, I recommend scheduling time, setting goals, assessing the odds, and lowering the bar.
Scheduling the work means that you won’t let something linger indefinitely. It also gives your brain permission to relax if you don’t absolutely need to focus on the action right now. You can rest knowing you have set aside time to dedicate to it.
Setting a goal is simply acknowledging that you want an outcome. It’s amazing how much relief you feel when you allow yourself to want something. Saying it out loud and writing it down are just ways to make it more concrete.
Then be honest about the odds. Not a prediction, just your best read on which way it’s going.
Lastly, lowering the bar is how I take fear out of the equation. When we are scared, we don’t see as clearly. Whatever you’re fearing, make the next step smaller. If it’s networking, start by listing a few people you know. If it’s assessing your finances, start with downloading your spending data from your bank account. Whatever it is, keep it small. You can work up to the larger, higher-stakes work once you’ve had enough small wins.
Take Action
After months of rumination, Beth has started naming her goals and scheduling time for small steps.
If you’re wondering if your job is no longer a fit, start here:
Schedule time: Clear space on your calendar to explore the actions below. Without time set aside, you won’t take the steps you need.
Goals: What do I want to get out of this job? Not what you wanted when you started, but what you want now.
Odds: What are signs that I’m going to get what I want or not? On balance, which way do I think it’ll go? This is an estimate. Not a crystal ball reading.
Lower the Bar: What’s the smallest next step I can take to test whether I should wait or start a search process? Small steps could include candid internal conversations, a review of your finances, or a quick set of chats with trusted confidantes.
You don’t have to do all of this this week, but if you have five minutes, you can start to schedule the key pieces. That’s how Beth is moving through them.
She knows it’s important because she’s seeing the signals. So she’s making time to assess it now, not later. You can, too.
Pay attention to the signals. My sandal didn’t give me a choice. Your job still might.
May you lead without limits,
Kathy
Paid Subscriber Guide & Live Call
The four questions above get you started.
My November Worksheet for paid subscribers, Stay, Go, or Decide What to Know Next, walks you through finishing: what matters to you now, what’s actually true about your role, and a decision you can put down. Even if that decision is “here’s what I need to find out first, and by when.”
Paid Subscriber Benefits page has a link to all worksheets.
We’ll be talking about it at our next Ask Me Anything live monthly call for paid subscribers on November 20th at 11am ET.
All calls are recorded, but only paid subscribers can access them. Come and bring your questions. Or submit them in advance — happy to make them anonymous when I address them.
You don’t need to wait any longer to assess your next move. Join as a Lead Without Limits paid subscriber and get the support you need, from other experienced leaders and from me.
Your future self will thank you.
“Indecision is simply a passive decision” is the line I’ll keep. Steven Levitt tested something close to it: thousands of people stuck on a major choice, often whether to quit a job, let a coin toss decide. Those whose coin said “change” were more likely to make the change, and six months later the people who had changed, especially those who quit, reported being happier. (The volunteers chose to take part, so it’s a signal rather than proof.) Your “choose to stay, on purpose and with a date to look again” reads like the healthy version of the same finding: the problem isn’t staying, it’s not choosing.